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[6-endo-trig Mode Cyclization to a Hydrindanone Using Samarium (II) Iodide]

[6-endo-trig Mode Cyclization to a Hydrindanone Using Samarium (II) Iodide]

Masakazu Sono

Yakugaku Zasshi. 2003 Aug;123(8):653-63.

PMID: 12931661

Abstract:

Samarium (II) iodide has been employed to promote the vinylogous pinacol coupling reaction of aldehyde to alpha, beta-unsaturated ketones. The diastereoselectivity of 6-endo-trig mode products was changed by the addition of a proton source and/or HMPA and by the reaction temperature. The stereochemistry of the hydrindanone was controlled by the coordinated samarium species, resulting in the cis-orientation in respect of the hydroxyl group at C-4 and the juncture proton at C-3a under mild reaction conditions. Coronafacic acid has been synthesized from a hydrindanone prepared by the cyclization reaction of the enone-aldehyde with samarium (II) iodide.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP32248434	Samarium(II) iodide		32248-43-4	Price

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